Dehydrohalogenation of hydrochlorofluorocarbons

Abstract

A dehydrohalogenation product includes a hydrochlorofluorocarbon mixture of a fluoroolefin of formula RCX═CZQ and a halofluoroalkane of formula RCXYCZQT. R is a perfluorinated alkyl group and X, Z, and Q are independently H or halogen. One of Y and T is H and the other is Cl, Br, or I. About 80% or greater of the hydrochlorofluorocarbon mixture is the fluoroolefin. The dehydrohalogenation product also includes a caustic agent and a solvent. In some embodiments, the dehydrohalogenation product is free of any catalyst, including any phase transfer catalyst.

What is claimed is: 
     
       1. A composition comprising:
 a hydrochlorofluorocarbon mixture comprising:
 a fluoroolefin of formula RCX═CZQ, wherein R is a perfluorinated alkyl group and X, Z, and Q are independently H or halogen; and 
 a halofluoroalkane of formula RCXYCZQT, wherein one of Y and T is H and the other is Cl, Br, or I; 
 wherein about 80% or greater of the hydrochlorofluorocarbon mixture is the fluoroolefin; 
 
 a caustic agent; and 
 a solvent. 
 
     
     
       2. The composition of  claim 1 , wherein the composition is free of any catalyst, including any phase transfer catalyst. 
     
     
       3. The composition of  claim 1 , wherein the caustic agent is selected from the group consisting of NaOH, KOH, LiOH, CsOH, Ca(OH) 2 , Zn(OH) 2 , Na 2 CO 3 , K 2 CO 3 , K 3 PO 4 , Na 3 PO 4 , KF, and CsF. 
     
     
       4. The composition of  claim 1 , wherein the solvent is an aqueous solvent. 
     
     
       5. The composition of  claim 4 , wherein the aqueous solvent is water. 
     
     
       6. The composition of  claim 1 , wherein the halofluoroalkane is CF 3 CHClCH 2 Cl and the fluoroalkene is CF 3 CCl═CH 2  or wherein the halofluoroalkane is CF 3 CH 2 CHCl 2  and the fluoroalkene is CF 3 CH═CHCl or wherein the halofluoroalkane is CF 3 CCl 2 CH 3  and the fluoroalkene is CF 3 CCl═CH 2  or wherein the halofluoroalkane is CF 3 CHFCH 2 Cl and the fluoroalkene is CF 3 CF═CH 2  or wherein the halofluoroalkane is CF 3 CClFCH 3  and the fluoroalkene is CF 3 CF═CH 2 . 
     
     
       7. The composition of  claim 1 , wherein one of Y and T is hydrogen and the other is chlorine. 
     
     
       8. The composition of  claim 1  further comprising an amine. 
     
     
       9. The composition of  claim 8 , wherein the amine is present at a molar ratio in the range of about 0.05 to about 3 with respect to the caustic agent. 
     
     
       10. The composition of  claim 8 , wherein the amine has the formula NR1R2R3 wherein R1, R2 and R3 are independently hydrogen, alkyl group, aryl, arylalkyl group, heterocyclic, heterocyclicalkyl, or N(R4)(R5)N(R6)(R7), wherein R4, R5, R6 and R7 are independently hydrogen, alkyl group, aryl, arylalkyl group, heterocyclic, or heterocyclicalkyl. 
     
     
       11. The composition of  claim 8 , wherein the amine is triethylamine. 
     
     
       12. The composition of  claim 1  further comprising ammonia. 
     
     
       13. The composition of  claim 1 , wherein the halofluoroalkane is CF 3 CHClCH 2 Cl (243db) and the fluoroolefin is CF 3 CCl═CH 2  (1233xf). 
     
     
       14. The composition of  claim 13  further comprising trans-CF 3 CH═CHCl (1233zd) and CF 3 CH═CH 2  (1243zf). 
     
     
       15. The composition of  claim 1 , wherein the caustic agent is present at a molar ratio in the range of about 0.01 to about 5 with respect to the hydrochlorofluorocarbon mixture. 
     
     
       16. The composition of  claim 1 , wherein about 97% or greater of the hydrochlorofluorocarbon mixture is the fluoroolefin. 
     
     
       17. The composition of  claim 1 , wherein the composition is a product of a dehydrohalogenation process. 
     
     
       18. The composition of  claim 1 , wherein the perfluorinated alkyl group is selected from the group consisting of —CF 3  and —CF 2 CF 3 . 
     
     
       19. The composition of  claim 1 , wherein the solvent comprises water and at least one additional solvent selected from the group consisting of methanol, ethanol, 1-propanol, 2-propanol, 1,3-butandiol, 1,2-butanediol, acetonitrile, acetaldehyde, acetone, ethylene glycol, propylene glycol, tetrahydrofuran, triethylene glycol, 1,3-propanediol, glycerol, and 1,4 dioxane. 
     
     
       20. The composition of  claim 1 , wherein the caustic agent is selected from the group consisting of an alkali metal oxide, an alkali metal hydroxide, an alkali metal amide, an alkaline earth metal oxide, an alkaline earth metal hydroxide, an alkaline earth metal amide, an alkali metal carbonate, an alkali metal phosphate, and an alkali metal carboxylate. 
     
     
       21. The composition of  claim 8 , wherein the amine is selected from the group consisting of a polyamine, a heterocyclic amine, hydrazine, a hydrazine derivative, and an aromatic amine. 
     
     
       22. The composition of  claim 1 , wherein the composition is free of any dehydrohalogenation catalyst, including any phase transfer catalyst. 
     
     
       23. The composition of  claim 15 , wherein the molar ratio is in the range of about 0.05 to about 1.5.